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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
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Ni-catalyzed direct reductive amidation via C-O bond cleavage
1Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007 Tarragona, Spain.
Journal of the American Chemical Society
|May 6, 2014
Summary
A new nickel-catalyzed reaction enables the synthesis of benzamides from simple starting materials. This reductive amidation method offers an unconventional approach using readily available catalysts.
Area of Science:
- Organic Chemistry
- Catalysis
- Synthetic Methodology
Background:
- Reductive amidation is a crucial transformation in organic synthesis.
- Traditional methods often require harsh conditions or complex catalysts.
- Developing efficient and accessible synthetic routes remains a key challenge.
Purpose of the Study:
- To develop a novel nickel-catalyzed reductive amidation reaction.
- To enable the synthesis of benzamides from C(sp2)-O and C(sp3)-O electrophiles and isocyanates.
- To establish an umpolung strategy for amide bond formation.
Main Methods:
- Utilizing nickel catalysts for reductive amidation.
- Employing isocyanates as nitrogen sources.
- Reacting C(sp2)-O and C(sp3)-O electrophiles under reductive conditions.
Main Results:
- Successful reductive amidation of various C(sp2)-O and C(sp3)-O electrophiles with isocyanates.
- Demonstration of an umpolung reactivity pattern.
- Formation of diverse benzamide products.
Conclusions:
- A novel and efficient Ni-catalyzed reductive amidation has been developed.
- This method provides an unconventional route to benzamides.
- The reaction utilizes simple starting materials and easy-to-handle nickel catalysts.
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